This invention relates to o-aminosulfonylphenyl acetic acid derivatives which are useful as plant growth regulants and herbicides.
French Pat. No. 1,468,747 discloses the following para-substituted phenylsulfonamides, useful as antidiabetic agents: ##STR1## where R=H, halogen, CF.sub.3 or alkyl.
Logemann et al., Chem. Ab., 53, 18052 g (1959), disclose a number of sulfonamides, including uracil derivatives and those having the formula: ##STR2## wherein R is butyl, phenyl or ##STR3## and R.sub.1 is hydrogen or methyl. When tested for hypoglycemic effect in rats (oral doses of 25 mg/100 g), the compounds in which R is butyl or phenyl were most potent. The others were of low potency or inactive.
Wojciechowski, J. Acta. Polon. Pharm. 19, P. 121-5 (1962) [Chem. Ab., 59 1633 e] describes the synthesis of N-[(2,6-dimethoxypyrimidin-4-yl)aminocarbonyl]-4-methylbenzenesulfonamide: ##STR4##
In U.S. Pat. No. 4,127,405, the following compounds are taught to have herbicidal activity: ##STR5## wherein R.sub.1 is ##STR6## R.sub.3 and R.sub.6 are independently hydrogen, fluorine, chlorine, bromine, iodine, alkyl of 1-4 carbon atoms, alkoxy of 1-4 carbon atoms, nitro, trifluoromethyl, cyano, CH.sub.3 S(O).sub.n -- or CH.sub.3 CH.sub.2 S(O).sub.n --;
R.sub.4 is hydrogen, fluorine, chlorine, bromine or methyl; PA1 R.sub.5 is hydrogen, fluorine, chlorine, bromine, methyl or methoxy; PA1 R.sub.7 is hydrogen, fluorine, chlorine, bromine, alkyl of 1-2 carbon atoms or alkoxy of 1-2 carbon atoms; PA1 R.sub.8 is hydrogen, methyl, chlorine or bromine; PA1 R.sub.9 and R.sub.10 are independently hydrogen, methyl, chlorine or bromine; PA1 W and Q are independently oxygen or sulfur; PA1 n is 0, 1 or 2; PA1 X is hydrogen, chlorine, bromine, methyl, ethyl, alkoxy of 1-3 carbon atoms, trifluoromethyl, CH.sub.3 S- or CH.sub.3 OCH.sub.2 -; and PA1 Z is methyl or methoxy; or their agriculturally suitable salts; provided that: PA1 R is H, F, Cl, Br, NO.sub.2, CF.sub.3, C.sub.1 -C.sub.3 alkyl or C.sub.1 -C.sub.3 alkoxy; PA1 R.sub.1 is H or C.sub.1 -C.sub.4 alkyl; PA1 R.sub.2 is H or CH.sub.3 ; PA1 R.sub.3 is H, C.sub.1 -C.sub.4 alkyl or OCH.sub.3 ; PA1 R.sub.4 is H or C.sub.1 -C.sub.4 alkyl; PA1 R.sub.3 and R.sub.4 can be taken together to form --(CH.sub.2).sub.4 --, --(CH.sub.2).sub.5 -- or --(CH.sub.2 CH.sub.2).sub.2 O; PA1 R.sub.8 is H, CH.sub.3 or OCH.sub.3 ; PA1 R.sub.10 is H, C.sub.1 -C.sub.4 alkyl, C.sub.3 -C.sub.4 alkenyl, CH.sub.2 CH.sub.2 Cl or CH.sub.2 CH.sub.2 OCH.sub.3 ; PA1 A is ##STR10## W is O or S; X is H, Cl, Br, CH.sub.3, CH.sub.2 CH.sub.3, C.sub.1 -C.sub.3 alkoxy, CF.sub.3, SCH.sub.3 or CH.sub.2 OCH.sub.3 ; PA1 Y is CH.sub.3 or OCH.sub.3 ; PA1 Z is N, CH, CCl, CBr, CCN, CCH.sub.3, CCH.sub.2 CH.sub.3, CCH.sub.2 CH.sub.2 Cl or CCH.sub.2 CH.dbd.CH.sub.2 ; PA1 Y.sup.1 is H, CH.sub.3, OCH.sub.3 or OCH.sub.2 CH.sub.3 ; and PA1 Q is O or CH.sub.2 ; and their agriculturally suitable salts; provided that: PA1 (1) Compounds of the generic scope wherein L is CO.sub.2 R.sub.10, W is O, Z is N, CH, CCl, CBr or CCH.sub.3, and R.sub.8 is H or CH.sub.3 ; PA1 (2) Compounds of Preferred (1) wherein Z is CH or N, X is CH.sub.3 or OCH.sub.3, and R.sub.1 and R.sub.2 are H; PA1 (3) Compounds of Preferred (2) wherein A is ##STR11## R.sub.8 is H and R is H; (4) Compounds of Preferred (3) wherein R.sub.10 is CH.sub.3 or CH.sub.2 CH.sub.3. PA1 2-[[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-aminosulfonyl]benzeneacetic acid, methyl ester; PA1 2-[[(4,6-dimethylpyrimidin-2-yl)aminocarbonyl]-aminosulfonyl]benzeneacetic acid, methyl ester; PA1 2-[[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]-aminosulfonyl]benzenea cetic acid, methyl ester; PA1 2-[[(4,6-dimethoxy-1,3,5-triazin-2-yl)aminocarbonyl]-aminosulfonyl]benzenea cetic acid, methyl ester; PA1 2-[[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)aminocarbonyl]aminosulfonyl]benz eneacetic acid, methyl ester; PA1 2-[[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-aminosulfonyl]benzeneacetic acid, ethyl ester; and PA1 2-[[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]-aminosulfonyl]benzenea cetic acid, ethyl ester. PA1 R, R.sub.1, R.sub.2 and R.sub.10 are as previously defined; PA1 provided that R.sub.10 cannot be H. PA1 (a) The compound of Formula II can be suspended or dissolved in an alkanol solvent, R.sub.12 OH, in the presence of at least two equivalents of alkoxide, OR.sub.12. The alkoxide can be added directly as alkali metal or alkaline earth metal alkoxide or can be generated by the addition to the alkanol solvent of at least two equivalents of a base capable of generating alkoxide from the solvent. Suitable bases include, but are not limited to, the alkali and alkaline earth metals, their hydrides and tert-butoxides. For example, when R.sub.12 is methyl, the compound of Formula II could be suspended or dissolved in methanol in the presence of two equivalents of sodium methoxide. Alternatively, two equivalents of sodium hydride could be used in place of the sodium methoxide. PA1 (b) The compound of Formula II can be suspended or dissolved in an inert solvent in the presence of at least two equivalents of alkoxide, OR.sub.12. Suitable inert solvents include, but are not limited to, acetonitrile, THF and dimethylformamide. The alkoxide may be added directly as alkali metal or alkaline earth metal alkoxide or may be generated from alkanol and a base as described in (a) above. For example, when R.sub.12 is methyl, the compound of Formula II could be suspended or dissolved in THF in the presence of two equivalents of sodium methoxide. Alternatively, two equivalents each of methanol and sodium hydride could be used instead of sodium methoxide.
(a) when R.sub.5 is other than hydrogen, at least one of R.sub.3, R.sub.4, R.sub.6 and R.sub.7 is other than hydrogen and at least two of R.sub.3, R.sub.4, R.sub.6 and R.sub.7 must be hydrogen; PA2 (b) when R.sub.5 is hydrogen and all of R.sub.3, R.sub.4, R.sub.6 and R.sub.7 are other than hydrogen, then all of R.sub.3, R.sub.4, R.sub.6 and R.sub.7 must be either chlorine or methyl; and PA2 (c) when R.sub.3 and R.sub.7 are both hydrogen, at least one of R.sub.4, R.sub.5 or R.sub.6 must be hydrogen. PA2 (1) when L is CONR.sub.3 R.sub.4, then Z is CH or N; PA2 (2) when R.sub.3 is OCH.sub.3, then R.sub.4 is CH.sub.3 ; and PA2 (3) when W is S, R.sub.8 is H.
In particular, the patent discloses orthosubstituted compounds wherein the substitution is C.sub.1 -C.sub.4 alkyl.
The presence of undesired vegetation causes substantial damage to useful crops, especially agricultural products that satisfy man's basic food needs, such as soybeans, corn, wheat and the like. The current population explosion and concomitant world food shortage demand improvements in the efficiency of producing these crops. Preventing or minimizing the loss of a portion of such valuable crops by killing, or inhibiting the growth of undesired vegetation is one way of improving this efficiency.
A wide variety of materials useful for killing, or inhibiting (controlling) the growth of undesired vegetation is available; such materials are commonly referred to as herbicides. The need exists, however, for effective herbicides that destroy or control weeds while not significantly damaging useful crops.
J. Heterocyclic Chemistry, 8, 947 (1971) discloses: ##STR7##
Chemische Berichte, 103, 1992 (1970) discloses: ##STR8##